Dimethylformamide → N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(thiazol-2-ylaminosulphonyl)phenyl]urea

HRID 2379345Notes

Reaction equation

HRID 2379345 reaction equation
C1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH3:18])[C:10](=[O:19])[CH:9]([NH:20][C:21]([O:23]C3C=CC([N+]([O-])=O)=CC=3)=O)[N:8]=2)CCCCC1.C(N([CH2:38][CH3:39])CC)C.CN(C)C=O.[S:45]1[CH:49]=[CH:48][N:47]=[C:46]1[NH:50][S:51]([C:54]1[CH:59]=[CH:58][CH:57]=[C:56]([NH2:60])[CH:55]=1)(=[O:53])=[O:52]>CO>[CH2:39]1[CH2:38][CH:7]([C:9]2([NH:20][C:21]([NH:60][C:56]3[CH:57]=[CH:58][CH:59]=[C:54]([S:51]([NH:50][C:46]4[S:45][CH:49]=[CH:48][N:47]=4)(=[O:53])=[O:52])[CH:55]=3)=[O:23])[N:8]=[CH:7][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]([CH3:18])[C:10]2=[O:19])[CH2:13][CH2:12][CH2:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 167883753-amino-N-(1,3-thiazol-2-yl)benzene-1-sulfonamideHCID 21480451HCID 21480451, compound

Product 1

HCID 57026685N-[3(R,S)-5-Cyclohexyl-2,3-dihydro-1-methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]N'-[3-(thiazol-2-ylaminosulphonyl)phenyl]urea

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from 5-cyclohexyl- 1,3-dihydro-1-methyl-3(R,S)-[(4-nitrophenyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (0.3 g, 0.69 mmol), triethylamine (96 μl, 0.69 mmol), dimethylformamide (6 ml) and 1-(thiazol-2-ylaminosulphonyl)-3aminobenzene (0.19 g, 0.76 mmol) using the procedure described in Example 11, Step 4. The product (125 mg, 33% ) was afforded as a cream solid after trituration with methanol. mp 230° C. (dec.). 1H NMR (360 MHz, D6 -DMSO) δ 0.84-0.96 (1H, m), 1.08-1.65 (7H, m), 1.71-1.81 (1H, m), 1.86-1.94 (1H, m), 2.88-2.96 (1H, m), 3.32 (3H, s), 5.06 (1H, d, J=8.2 Hz), 6.80 (1H, d, J=4.6 Hz), 7.22 (1H, d, J=4.6 Hz), 7.28-7.42 (5H, m), 7.55 (1H, d, J=7.4 Hz), 7.64 (1H, dd, J=7.1 and 7.0 Hz), 7.75 (1H, d, J=7.9 Hz), 7.98 (1H, s), 9.30 (1H, s), 12.63 (1H, brs).

Sources & evidence

ORD record
ord-3d50d079c6944e22853698f091f71c64
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

Loading…